There are pockets of time throughout Orioles' history that, in retrospect, can be viewed as watershed moments: The Frank Robinson trade in 1965, the Glenn Davis trade in 1991, the Erik Bedard trade in 2008.

The July, 1996 non-deals of Bobby Bonilla and David Wells sent the Orioles on one path; the fire sale of 2000, which yielded Melvin Mora and a raft-load of baseball driftwood, sent them on another.

There's no gift of hindsight here, but the next few weeks and months have the feel of another potential seismic shift. These Orioles are at a crossroads, and the destination could become clearer by the end of this road trip. They play three at Yankee Stadium and three more at Tropicana Field before heading home with less than a week remaining before the July 31 nonwaiver trade deadline.

To properly defend their American League East crown, this club could really use a rotation ace, an everyday left fielder with on-base capabilities and a shutdown left-handed reliever.

Watch for rumors and you'll see major names connected to the Orioles in the next 10 days: Justin Upton, Johnny Cueto, Cole Hamels, Jay Bruce, Carlos Gomez, etc. It's wonderful to dream, but the reality is there has to be interest on both sides.

The sense within the organization and within the industry is that the Orioles have no chance of landing a coveted trade chip because they have nothing to deal in comparison to other contenders. They have no true centerpieces — young prospects with major upside that can contribute now or relatively soon — to give a selling club, unless they parted with Manny Machado, Jonathan Schoop or Kevin Gausman, which they won't.

Arm injuries have pushed top pitching prospects Dylan Bundy and Hunter Harvey to the back of the shelf; other organizations might still gamble on them, but not as centerpieces to a Cueto deal, for instance. Third base prospect Jomar Reyes and catcher Chance Sisco may one day be viewed as centerpieces, but aren't there yet. Minor league pitchers Tyler Wilson, Mike Wright and Mychal Givens are intriguing, but more so for a lesser deal.

And that's what most expect to happen with the Orioles this month or in August. Duquette will make a move or moves to fill holes, but they'll be under-the-radar acquisitions: Think the 2015 version of Scott Feldman or Alejandro De Aza or Francisco Rodriguez.

Duquette has stressed several times that he will make this team better this summer, but better is in the eye of the beholder. Remember, it took lefty Eduardo Rodriguez, the Orioles' No. 3 prospect last year, just to get excellent reliever Andrew Miller last July. This organization doesn't have a Rodriguez-type in 2015.

Then there's the elephant in the clubhouse: The seven pending free agents that the Orioles have at season's end. If the Orioles implode in the next week, the temptation to move some for younger pieces will grow exponentially given the lack of perceived depth in this organization.

Three of those free agents, catcher Matt Wieters, slugger Chris Davis and left-hander Wei-Yin Chen, likely will be made one-year qualifying offers of $16 million-plus this offseason. All are represented by agent Scott Boras, who abhors the qualifying offer process, so one can assume that each member of the trio would reject the offers and, if they sign elsewhere, the Orioles would receive supplemental first-round picks in the 30-to-40 range next June as compensation.

The other four — pitchers Darren O'Day, Tommy Hunter and Bud Norris, and infielder/outfielder Steve Pearce — would fetch varying levels of return if dealt this summer, but won't be saddled with qualifying offers. The only incentive in keeping them in 2015 is to try and win now.

Here's a list of the Orioles' pending free agents, ordered based on who is most likely to re-sign with the team before next season. Call it slightly educated speculation.

And know this: There is a growing sense within the organization that the Orioles will keep none of these guys — or one or two at most. If that's the case, the next few months will, indeed, register as franchise-defining.

It may be surprising that Pearce, who is struggling after his breakout campaign in 2014, would be atop this list. But there are several factors at play. The Orioles don't know if 24-year-old Christian Walker is ready to start at first base if Davis doesn't return. Pearce is good insurance there, or at various other positions. He's a Buck Showalter guy: Versatile, hard-working and he never complains about playing time. The 32-year-old has been with five different organizations, and has finally found a home with a manager he trusts. That security and familiarity may be more important to him than a slightly higher paycheck. And that brings us to the most critical thing here: Pearce, who makes $3.7 million this year, should be relatively affordable to extend.

From afar, O'Day looks like a slam-dunk to return. The sidearmer has been one of the best set-up men in baseball since joining the Orioles in 2012. He's the unquestioned bullpen leader, and, at 32, is getting better with age. He also makes his offseason home in the area; his wife, Liz, is a Washington, D.C. correspondent with Fox News. But O'Day is a 2015 All-Star and the profile of the late-inning non-closer is burgeoning thanks to the success of teams like the Orioles and the Kansas City Royals. Translation: Free agent relievers are getting paid. Problem is the Orioles usually don't give out three-year deals to relievers. They did that before the 2007 season with Danys Baez ($19 million), Jamie Walker ($12 million) and Chad Bradford ($10.5 million) and none lasted all three seasons with the club — such is the mercurial nature of relief pitching. Since the Orioles have already received 3 1/2 great years from O'Day, they may assume the down trend is coming. A good starting point comp is sidearmer Joe Smith, who signed a three-year $15.75 million deal with the Los Angeles Angels two offseasons ago. Smith wasn't as accomplished as O'Day, though Smith is 17 months younger. There haven't been any serious attempts to extend O'Day and the Orioles don't seem to pay extra for clubhouse chemistry. So this may be another example of the market outpricing what the Orioles believe is fair value.

Bottom line: There's no reason O'Day shouldn't be back, but if the Orioles wait too long, some team is going to blow away their offer.

3. Catcher Matt Wieters

Stats: .258/.282/.443; 3 homers, 11 RBIs, 97 at-bats

The gut feeling is Wieters is gone. It's been a while — Brian Roberts before the 2009 season — since the Orioles shelled out big money to a homegrown player within a season of free agency. And the four-year, $40 million extension that Roberts agreed to, which ended up being an organizational albatross, isn't close to what Wieters can command, even after missing a year due to Tommy John surgery. Consider that catcher Brian McCann signed a five-year, $85 million deal with the New York Yankees before the 2014 season and he was slightly older than the 29-year-old Wieters will be when he signs a new deal. Wieters still must prove he is healthy and can catch mostly every day. But if he does, there could be a pretty impressive bidding war for his services, especially with Boras leading the negotiations. The one thing in the Orioles' favor is that Wieters is not the kind to chase every last dollar. He's low-key, and focused on a comfortable, winning environment. Plus, he has excellent relationships with Showalter, catching instructor John Russell and backup Caleb Joseph. That means something to Wieters. But the Atlanta Braves are searching for a long-term solution at catcher also. Wieters grew up in South Carolina rooting for the Braves and currently lives in Atlanta, where he and his wife went to college. His parents, who often drive to Baltimore for games, would have a shorter commute from South Carolina. Since the Braves are trying to build a contender for their new stadium, they'll be aggressive with the players they want, like they were with Wieters' buddy Nick Markakis. Atlanta won't be the only team wooing Wieters, but it seems like a perfect fit.

Bottom line: The Orioles would love to have Wieters spend his full career in Baltimore, but it's a stretch to see them spend what it will take to keep aggressive suitors at bay.

The case can be made that Chen is the most important of the Orioles' pending free agents. He's the rotation's only lefty and has been the club's best pitcher this year. He turns 30 Tuesday and should have plenty of good seasons remaining. Baltimore is the only big-league city he has known, and he fits in exceptionally well with his teammates. But the free agent market for starting pitching continues to be outrageous — remember, the Orioles paid $50 million for Ubaldo Jimenez in 2014 — and the Boras-repped Chen should cash in. You also have to wonder if some of the goodwill built over the years with Chen took a significant hit when the club sent him to the minors earlier this year as part of its continual roster shuffle.

Bottom line: The Orioles got four years out of Chen for roughly $15.5 million. He'll no longer be a bargain, so expect him to sign with the highest bidder.

5. 1B/RF Chris Davis

Stats: .238/.320/.463; 19 homers, 53 RBIs, 320 at-bats

Davis has said repeatedly that he'd like to remain an Oriole, but as his career has progressed here, that possibility becomes less and less a reality. Now, it would be a surprise if he is in Baltimore in 2016 and it wouldn't be shocking if he's dealt this month if the Orioles fell out of contention since he could fetch a strong return. It's something that has been discussed internally, but the sense from within is the team needs his power bat to contend. After his tremendous 53-homer season in 2013, Davis has been criticized in Baltimore for alarming strikeout totals and low average. But he's only 29 and is on pace for his fourth straight season of 26 or more homers. There's not a team in baseball that couldn't use his power, and someone will pay dearly for it. His free-agent value has probably spiked with his move to right field, proving that he can play multiple positions adequately.

Bottom line: Two years ago he seemed like a club cornerstone. But if the Orioles really wanted him back a deal already would have happened. He'll get a lot more money elsewhere.

Fans have used him as a whipping boy at times in his four-plus seasons with the Orioles, but the fact is he's a competent big-league set-up man. And finding one at his age (29) with his experience (over 260 big league games, including 75 starts) and his command (34 walks in 186 2/3 innings since the 2013 season began) isn't easy. So a three-year deal is probably in his future. He also could be traded this month or in August if the Orioles stumble.

Bottom line: He'll be missed when he's gone, but, statistically, the Orioles believe they can replace him with someone much cheaper.

This has gone poorly for all involved in 2015. Norris won 15 games last year as a big part of the division winner. But he's struggled since spring training and lost his rotation spot. Although his power slider can be a bullpen asset, no one's happy with a $9 million mop-up man. The best-case scenario for Norris is that the Orioles orchestrate a salary-dump trade before he becomes an offseason decision.

Bottom line: He's gone, whether it's this month, next month or in the offseason.